Hydrochloric Acid → HCID 18770380, compound

The crude crystals (17.1 g) of di-tert-butyl 2,2- bis[(4-pyridyl)methyl]malonate synthesized by the above process were dissolved in trifluoroacetic acid (90 ml), and the solution was stirred at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure, and the resultant concentrated residue was heated for 20 minutes in a bath controlled at 200° C. and then dissolved in methanol (170 ml). A 4N hydrogen chloride in ethyl acetate (100 ml; 400 mmol) was added to the solution, and the mixture was stirred for 2 hours and then concentrated under reduced pressure. The resultant concentrated residue was made basic by addition of aqueous 2.5N sodium hydroxide and extracted with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resultant crude oil was purified by column chromatography on silica gel, thereby obtaining 6.0 g (yield: 51%) of methyl 2,2-bis[(4-pyridyl)methyl]acetate as a colorless oil.

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. temperaturethe resultant concentrated residue was heated for 20 minutes in a bath
3. customcontrolled at 200° C.
4. dissolutiondissolved in methanol (170 ml)
5. stirringthe mixture was stirred for 2 hours
6. concentrationconcentrated under reduced pressure
7. additionThe resultant concentrated residue was made basic by addition of aqueous 2.5N sodium hydroxide
8. extractionextracted with chloroform
9. washThe organic layer was washed with saturated brine
10. dry with materialdried over anhydrous sodium sulfate
11. concentrationconcentrated under reduced pressure
12. customThe resultant crude oil was purified by column chromatography on silica gel

ORD record

ord-18c4feafeaf9474e814f785e620bb333

Source dataset

uspto-grants-2002_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06448242B1